73086-81-4

Basic information

• Product Name: Pyridinium, 2,4,6-triphenyl-1-(2-propenyl)-, tetrafluoroborate(1-)
• CAS NO: 73086-81-4
• Molecular Formula: C26H22N.BF4
• Molecular Weight: 435.272
• Mol File: 73086-81-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Pyridinium, 2,4,6-triphenyl-1-(2-propenyl)-, tetrafluoroborate(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridinium, 2,4,6-triphenyl-1-(2-propenyl)-, tetrafluoroborate(1-)(73086-81-4)
• EPA Substance Registry System: Pyridinium, 2,4,6-triphenyl-1-(2-propenyl)-, tetrafluoroborate(1-)(73086-81-4)

Safety Data

• Hazardous Substances Data: 73086-81-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 94-41-7 benzalacetophenone 

Downstream Products

• 72863-35-5 7-phenylhept-1-en-4-one 
• 85234-21-5 1-(4-methoxyphenyl)but-3-en-1-one 
• 202932-64-7 1-phenyl-5-hexen-3-one 
• 1227403-16-8 1-allyl-2-(phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1415029-93-4 1-methoxy-4-(pent-4-en-1-yn-1-yl)benzene 
• 74248-47-8 N-allyl-2,6-dimethylaniline 
• 40637-56-7 dimethyl allylmalonate 
• 35357-77-8 dimethyl bisallylmalonate 
• 696-57-1 N-allylmorpholine 
• 580-35-8 2,4,6-triphenylpyridine 
• 87803-29-0 cis-1-(1-Propenyl)-2,4,6-triphenylpyridinium tetrafluoroborate 
• 85018-20-8 trans-1-(1-Propenyl)-2,4,6-triphenylpyridinium tetrafluoroborate 
• 87803-41-6 6-Hydroxy-4-methyl-1,6,7-triphenyl-2-azoniabicyclo<3.3.0>octa-2,7-diene tetrafluoroborate 
• 87803-44-9 2-(2-Benzoyl-1-methylethyl)-3,5-diphenylpyrrole 

Relevant articles and documents

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.

A concise preparation of η3-allylpalladium tetrafluoroborates from N-allylpyridinium tetrafluoroborates [1]

N-allyl-2,4,6-triphenylpyridinium tetratluoroborates react with bis(dibenzylideneacetone) palladium(0) and two equivalents of triphenylphosphine, or one equivalent of diphosphine, to give η3-allyl palladium tetrafluoroborates, 2,4,6-triphenylpyridine acting as neutral leaving group. Springer-Verlag Iberica 1996.